Hydrochloric Acid → HCID 68537270, 화합물

HRID 1992866노트

반응식

HRID 1992866 반응식
[CH3:1][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([O:16]COC)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:3].Cl>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:3][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([OH:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:1]

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 68539388HCID 68539388, 화합물

생성물 1

HCID 68537270HCID 68537270, 화합물수율 99.3%

시약·촉매·용매 3

HCID 962Water용매HCID 312751,4-Dioxane용매2회HCID 57417360Sodium chloride; water용매

실험 절차

3-(1-Methylethyl)-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenyl naphthalene (71) (0.42 g, 1.24 mmol) was dissolved in dioxane (8 mL). 4 M HCl in dioxane (8 mL) was added and the reaction mixture was stirred at room temperature for 30 min. The mixture was diluted with water (25 mL) and brine (25 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1) to give 0.36 g (98%) of the title compound (72) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.16 (d, J=6.8 Hz, 6H), 2.79 (sept, J=6.8 Hz, 1H), 3.93 (s, 3H), 5.08 (s, 1H), 7.05-7.12 (m, 2H), 7.30 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.50 (m, 1H), 7.50-7.58 (m, 2H), 8.07 (d, J=9.0 Hz, 1H). LCMS (APCI): m/z 293 (M+H)+.

후처리

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product as a light yellow oil
  7. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1)

출처 및 근거

ORD 기록
ord-6db98b2e20b54d01a3ab8564f16b018a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

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